Prior research argues that behaviorally complex managers may contribute to an organizational unit’s ability to become ambidextrous. While some scholars suggest that such managers engage directly in the reconciliation of exploration and exploitation, others propose that they foster both activities indirectly by framing an ambidextrous behavioral context for all employees. We hypothesize that these direct and indirect processes are not independent alternatives, but are interrelated and contribute jointly to unit-level ambidexterity. Based on two quantitative data sets, we find that managers in SMEs have a direct and indirect effect on unit-level ambidexterity, while those in larger corporations’ business units only have an indirect effect. Theoretically, our study extends and reconciles the literature on managerial and contextual ambidexterity, as well as that on individual-level and unit-level ambidexterity. The insight that the effectiveness of different paths to ambidexterity appears to depend on the type of organization or unit under study, is discussed at length.